Citation: Xiao-Bo WANG, Xiao-Qi YU, Xue-Lei HU. Synthesis, Crystal Structures, DNA Cleavage and DNA-binding Studies of Ho(Ⅲ) and Er(Ⅲ) Complexes Based on Macrocyclic Schiff Base[J]. Chinese Journal of Structural Chemistry, ;2020, 39(6): 1103-1111. doi: 10.14102/j.cnki.0254-5861.2011-2601 shu

Synthesis, Crystal Structures, DNA Cleavage and DNA-binding Studies of Ho(Ⅲ) and Er(Ⅲ) Complexes Based on Macrocyclic Schiff Base

Xiao-Bo WANG ^{a, b,,} ,
Xiao-Qi YU ^c ,
Xue-Lei HU ^a,,

a.
School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan 430205, China
b.
School of Pharmacy, Hubei University of Science and Technology, Xianning, Hubei 437100, China
c.
Hubei Geological Research Laboratory, Wuhan 430034, China

Corresponding author: Xiao-Bo WANG, eas7on@163.com Xue-Lei HU, huxuelei@mail.wit.edu.cn
Received Date: 12 September 2019
Accepted Date: 5 December 2019

Fund Project: the Natural Science Foundation of Hubei Province 2018CFB323

Figures(5)

Two novel macrocyclic Schiff base complexes [LnL(PhCOO)(CH₃OH)](ClO₄)₂·(CH₃OH)₂ (Ln = Ho, 1; Ln = Er, 2), in which L denotes the macrocyclic ligand, were synthesized via condensation of 2, 6-diformyl-4-methyl-phenol and 1, 3-diamino-2-propanol by employing benzoate as the second ligand. Their crystal structures were determined by X-ray diffraction, which showed that both complexes belong to a monoclinic system with space group P2₁/c. The coordination polyhedron displayed a distorted bicapped trigonal prism with the coordination number of eight. Both complexes efficiently cleaved supercoiled DNA to its nicked circular form. The UV-vis absorption results and ethidium bromide (EB) fluorescence spectra indicated that the complexes bind to CT-DNA in an intercalative mode, with K_sq values to be 11830 and 10560, respectively.
- macrocyclic Schiff base,
- crystal structure,
- CT-DNA,
- pBR 322,
- fluorescence spectrum
1. [1]
  Hu, D. D.; Zhang, Y. Y.; Yang, H. J.; Lin, J.; Wu, T. Structural transformation of selenidostannates from 1D to 0D and 2D via a stepwise amine-templated assembly strategy. Dalton Trans. 2017, 23, 7534–7539.
2. [2]
  Me, Y.; Xing, Y. H.; Wang, Z.; Zhao, H. Y.; Zeng, X. Q.; Ge, M. F.; Niu, S. Y. Synthesis, crystal structure and photoelectric property of two novel coordinated complexes constructed by 4, 4΄-bipyridine and sebacic acid. Inorg. Chem. Commun. 2009, 10, 975–977.
3. [3]
  Liu, X.; Li, B.; Xu, Y.; Li, Z. Q.; Zhang, Y.; Ding, Z. J.; Cui, H.; Wang, J.; Hou, H. B.; Li, H. R. A highly selective lanthanide-containing probe for ratiometric luminescence detection of an anthrax biomarker. Dalton Trans. 2019, 22, 7714–7719.
4. [4]
  Yang, Y. L.; Wang, P. Y.; Lu, L. F.; Fan, Y.; Sun, C. X.; Fan, L. L.; Xu, C. J.; El-Toni, A. M.; Alhoshan, M.; Zhang, F. Small-molecule lanthanide complexes probe for second near-infrared window bioimaging. Anal. Chem. 2018, 13, 7946–7952.
5. [5]
  Aletti, A. B.; Gillen, D. M.; Gunnlaugsson, T. Luminescent/colorimetric probes and (chemo-) sensors for detecting anions based on transition and lanthanide ion receptor/binding complexes. Coord. Chem. Rev. 2018, SI, 98–120.
6. [6]
  Urbanovsky, P.; Kotek, J.; Carniato, F.; Botta, M.; Hermann, P. Lanthanide complexes of DO3A-(dibenzylamino)methylphosphinate: effect of protonation of the dibenzylamino group on the water-exchange rate and the binding of human serum albumin. Inorg. Chem. 2019, 8, 5196–5210.
7. [7]
  Clough, T. J.; Jiang, L. J.; Wong, K. L.; Long, N. J. Ligand design strategies to increase stability of gadolinium-based magnetic resonance imaging contrast agents. Nat. Commun. 2019, 10, 1420, 1–14.
8. [8]
  Zhang, S. R.; Malloy, C. R.; Sherry, A. D. MRI thermometry based on PARACEST agents. J. Am. Chem. Soc. 2005, 50, 17572–17573.
9. [9]
  Kaczmarek, M. T.; Zabiszak, M.; Nowak, M.; Jastrzab, R. Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity. Coord. Chem. Rev. 2018, 370, 42–54. doi: 10.1016/j.ccr.2018.05.012
10. [10]
  Reji, T. F. A. F.; Pearl, A. J.; Rosy, B. A. Synthesis, characterization, cytotoxicity, DNA cleavage and antimicrobial activity of homodinuclear lanthanide complexes of phenylthioacetic acid. J. Rare Earth 2013, 10, 1009–1016.
11. [11]
  Singg, K.; Srivastava, P.; Patra, A. K. Binding interactions with biological targets and DNA photocleavage activity of Pr(Ⅲ) and Nd(Ⅲ) complexes of dipyridoquinoxaline. Inorg. Chim. Acta 2016, 451, 73–81. doi: 10.1016/j.ica.2016.07.003
12. [12]
  Chandra, S.; Agrawal, S. Spectroscopic characterization of lanthanoid derived from a hexadentate macrocyclic ligand: study on antifungal capacity of complexes. Spectrochim. Acta A 2014, 124, 564–570. doi: 10.1016/j.saa.2014.01.042
13. [13]
  Li, Y.; Yang, Z. Y. DNA-binding properties and antioxidant activity of lanthanide complexes with the Schiff base derived from 3-carbaldehyde chromone and isonicotinyl hydrazine. J. Coord. Chem. 2010, 11, 1960–1968.
14. [14]
  Bruker. SMART, SAINT, SADABS and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA 2000.
15. [15]
  Sheldrick, G. M. SHELXT 2014, New Small Molecule (SM) Structure Solution Program. University of Göttingen, Germany 2014.
16. [16]
  Koike, T.; Takamura, M.; Kimura, E. Role of zinc(Ⅱ) in β-lactamase Ⅱ: a model study with a zinc(Ⅱ)-macrocyclic tetraamine (1, 4, 7, 10-tetraazacyclododecane, cyclen) complex. J. Am. Chem. Soc. 1994, 116, 8443–8449. doi: 10.1021/ja00098a002
17. [17]
  Li, Q. X.; Wang, W. L.; Meng, X. G. A novel copper(Ⅱ) complex of asymmetrically N-functionalized 1, 4, 7-triazacyclononane ligand: syntheses, structure, electrochemical, property and biological activities. Chin. J. Struct. Chem. 2018, 6, 878–886.
18. [18]
  Liu, Y. J.; Mei, W. J.; Lu, J. Z.; Zhao, H. J.; He, L. X.; Wu, F. H. Ruthenium(Ⅱ) complexes of 2-(20-pyridyl)naphthaoimidazole: synthesis, characterization and DNA-binding studies. J. Coord. Chem. 2008, 20, 3213–3224.
19. [19]
  Mondal, S.; Pakhira, B.; Blake, A. J.; Brew, M. G. B.; Chattopadhyay, S. K. Co(Ⅲ) and Ni(Ⅱ) complexes of an anthracene appended aroyl hydrazone: synthesis, crystal structures, DNA binding and catecholase activity. Polyhedron 2016, 117, 327–337.
20. [20]
  Hu, X. L.; Chen, Z.; Qiu, L.; Zhao, Y. D.; Pan, Z. Q. Characterization, crystal structure and luminescence properties of a new europium(Ⅲ) complex with macrocyclic ligand derived from 2, 6-diformyl-4-methylphenol and diethylenetriamine. J. Rare Earth 2008, 6, 795–799.
21. [21]
  Boger, D. L.; Fink, B. E.; Brunette, S. R.; Tse, W. C.; Hedric, M. P. A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. J. Am. Chem. Soc. 2001, 25, 5878–5891.
22. [22]
  del Mundo, I. M. A.; Siters, K. E.; Fountain, M. A.; Marrow, J. R. Structural basis for bifunctional zinc(Ⅱ) macrocyclic complex recognition of thymine bulges in DNA. Inorg. Chem. 2012, 9, 5444–5457.
23. [23]
  Akbay, N.; Seferoglu, Z.; Goekoglu, E. Interactions of two ethidium derivatives with calf thymus DNA and serum albumins using fluorescence quenching method. Curr. Anal. Chem. 2010, 4, 334–340.
24. [24]
  Azab, H. A.; Kamel, R. M. Binding of chlorfenvinphos and malathion with DNA and their detection using new sensitive luminescent Tb(Ⅲ) complex probe. J. Lumin. 2016, SI, 671–678.
1. [1]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
2. [2]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
3. [3]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
4. [4]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
5. [5]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
6. [6]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
7. [7]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
8. [8]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
9. [9]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
10. [10]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
11. [11]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
12. [12]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
13. [13]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
14. [14]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
15. [15]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
16. [16]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
17. [17]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
18. [18]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
19. [19]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
20. [20]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(297)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142